| 100% | LIONELRICHIE | 12 | Singer with five #1 songs in the 1980s, including "All Night Long" (2 wds.) |
| 92% | LIONELRICHIE | 12 | Singer with five No. 1 songs in the 1980s, including "All Night Long (All Night)" (2 wds.) |
| 68% | GEORGEMICHAEL | 13 | Singer with eight #1 songs in the 1980s, including "Faith" (2 wds.) |
| 66% | GEORGEMICHAEL | 13 | Singer with eight No. 1 songs in the 1980s, including "Faith" (2 wds.) |
| 65% | STEVIEWONDER | 12 | Singer with four #1 songs in the 1980s, including "I Just Called to Say I Love You" (2 wds.) |
| 63% | STEVIEWONDER | 12 | Singer with four No. 1 songs in the 1980s, including "I Just Called To Say I Love You" (2 wds.) |
| 52% | LIONELRICHIE | 12 | Singer in the Commodores whose solo hits include "All Night Long (All Night)": 2 wds. |
| 48% | VANMORRISON | 11 | Rock singer with the 1971 song "Wild Night": 2 wds. |
| 45% | PETERCETERA | 11 | Singer with the 1986 #1 song “Glory of Love”: 2 wds. |
| 44% | PHILCOLLINS | 11 | Singer with the 1988 #1 song “Groovy Kind of Love”: 2 wds. |
| 44% | CAMILACABELLO | 13 | Pop singer with the hit song "Crying in the Club" (2 wds.) |
| 43% | MICHAELJACKSON | 14 | Singer with the most #1 Billboard Hot 100 hits (9) during the 1980s: 2 wds. |
| 42% | ERICCLAPTON | 11 | "I Shot the Sheriff" singer with the 1992 song "Tears in Heaven": 2 wds. |
| 41% | BILLWITHERS | 11 | Singer with the 1971 song "Ain't No Sunshine": 2 wds. |
| 41% | KIDROCK | 7 | Rap and country singer with the song "Bawitdaba": 2 wds. |
| 41% | JUSTINBIEBER | 12 | "Yummy" singer with the 2021 #1 song at 16-Across and the #1 album at 44-Across: 2 wds. |
| 40% | PAULMCCARTNEY | 13 | English bassist/singer in the Beatles whose solo hits include "No More Lonely Nights": 2 wds. |
| 40% | SHEENAEASTON | 12 | "Strut" singer who Prince encouraged and collaborated with in the 1980s: 2 wds. |
| 40% | CASSADEEPOPE | 12 | Pop singer with the hit song "Wasting All These Tears" (2 wds.) |
| 40% | MAYARUDOLPH | 11 | "Up All Night" actress who performed with the band The Rentals: 2 wds. |
| 39% | DIANAROSS | 9 | Singer in the Supremes whose solo hits include "Upside Down": 2 wds. |
| 39% | STRANGERTHINGS | 14 | Netflix series set in the 1980s in which single mom Joyce Byers contends with a supernatural monster: 2 wds. |
| 39% | STEVIEWONDER | 12 | "Sir Duke" singer who debuted songs on the Hot 100 in five different decades: 2 wds. |
| 39% | HUNTERHAYES | 11 | Singer with the #1 country single "Wanted": 2 wds. |
| 38% | JOHNLEGEND | 10 | Singer with the 2020 love song "Bigger Love" (2 wds.) |
| 38% | DEMILOVATO | 10 | Singer with the 2020 love song "I Love Me" (2 wds.) |
| 38% | JOHNLEGEND | 10 | "All of Me" singer who wrote a song in "SpongeBob SquarePants: The Broadway Musical": 2 wds. |
| 38% | ALBERTPUJOLS | 12 | Former Cardinals slugger tied for third place with five grand slam home runs in the 2009 season: 2 wds. |
| 38% | STEVIEWONDER | 12 | American singer with 25 Grammy Awards famous for his song "You Are the Sunshine of My Life": 2 wds. |
| 37% | KATYPERRY | 9 | Starting in 2010, pop singer with a song in the top 10 of the Billboard Hot 100 for 69 consecutive weeks: 2 wds. |